1,2-Dihydro-1-hydroxy-2,3,1-benzodiazaborine Bearing an Acridine Moiety as a Circular Dichroism Probe for Determination of Absolute Configuration of Mono-Alcohols

Shunsuke Shimo; Kohei Takahashi; Nobuharu Iwasawa

doi:10.1002/chem.201900350

1,2-Dihydro-1-hydroxy-2,3,1-benzodiazaborine Bearing an Acridine Moiety as a Circular Dichroism Probe for Determination of Absolute Configuration of Mono-Alcohols

Chemistry. 2019 Mar 12;25(15):3790-3794. doi: 10.1002/chem.201900350. Epub 2019 Feb 18.

Authors

Shunsuke Shimo¹, Kohei Takahashi¹, Nobuharu Iwasawa¹

Affiliation

¹ Department of Chemistry, Tokyo Institute of Technology, O-okayama, Meguro-ku, Tokyo, 152-8551, Japan.

PMID: 30689223
DOI: 10.1002/chem.201900350

Abstract

A new chiral probe molecule for mono-alcohols is developed by using 1,2-dihydro-1-hydroxy-2,3,1-benzodiazaborine (DAB) bearing an acridine moiety 1. In the presence of mono-alcohols, DAB 1 forms borate 2 by boronic ester formation, followed by coordination of the acridine moiety to the boron atom. Borate 2 has a chiral center on the boron atom and works as a stereodynamic circular dichroism (CD) probe molecule for chiral mono-alcohols based on the π-π interaction between the acridine moiety and the carbon-carbon unsaturated moiety on mono-alcohols.

Keywords: CD probe; benzodiazaborine; boron; chiral mono-alcohols; circular dichroism.

Grants and funding

15H05800/Japan Society for the Promotion of Science